Phenylmethyl 4-((6,7-dihydro[1,4]dioxino[2,3-c]pyridazin-3-ylmethyl){[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinecarboxylate → 1,1-Dimethylethyl (6,7-dihydro[1,4]dioxino[2,3-c]pyridazin-3-ylmethyl)4-piperidinylcarbamate

HRID 656983Notes

Reaction equation

HRID 656983 reaction equation
[N:1]1[C:6]2[O:7][CH2:8][CH2:9][O:10][C:5]=2[CH:4]=[C:3]([CH2:11][N:12]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:13]2[CH2:18][CH2:17][N:16](C(OCC3C=CC=CC=3)=O)[CH2:15][CH2:14]2)[N:2]=1>C(O)C.[Pd]>[N:1]1[C:6]2[O:7][CH2:8][CH2:9][O:10][C:5]=2[CH:4]=[C:3]([CH2:11][N:12]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:29](=[O:30])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[N:2]=1

Participants

4

Reactant 1

HCID 68992990Phenylmethyl 4-((6,7-dihydro[1,4]dioxino[2,3-c]pyridazin-3-ylmethyl){[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinecarboxylate

Product 1

HCID 866353301,1-Dimethylethyl (6,7-dihydro[1,4]dioxino[2,3-c]pyridazin-3-ylmethyl)4-piperidinylcarbamateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Phenylmethyl 4-((6,7-dihydro[1,4]dioxino[2,3-c]pyridazin-3-ylmethyl) {[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinecarboxylate (11.89 g. 25 mmol) in ethanol (90 ml) was hydrogenated with 10% palladium on charcoal (aqueous paste, 2 g) for 21 h. The mixture was filtered and evaporated to give a white solid (8.5 g, 97%).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-8c54f8abe94546d5bf09cc9faea1329f
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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